6-(4-Methoxy-phenyl)-6H,7H-chromeno[4,3-b]chromene | 850152-09-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 6-(4-Methoxy-phenyl)-6H,7H-chromeno[4,3-b]chromene
• 英文别名: 6H,7H-[1]Benzopyrano[4,3-b][1]benzopyran, 6-(4-methoxyphenyl)-；6-(4-methoxyphenyl)-6,7-dihydrochromeno[3,2-c]chromene
• CAS: 850152-09-9
• 化学式: C₂₃H₁₈O₃
• 分子量: 342.394
• InChiKey: SBCYVBUSCMLKNV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-(4-Methoxy-phenyl)-6H,7H-chromeno[4,3-b]chromene 在 palladium on activated charcoal 氢气 作用下， 以 四氢呋喃 为溶剂， 以50%的产率得到6-(4-Methoxy-phenyl)-6a,12a-dihydro-6H,7H-chromeno[4,3-b]chromene
  参考文献：
  名称：

  Homopterocarpanes as bridged triarylethylene analogues: synthesis and antagonistic effects in human MCF-7 breast cancer cells

  摘要：

  A series of new compounds structurally derived from 6a,12a-dihydro-6H,7H-[1]-benzopyran-[4,3-b]-benzopyran (homopterocarpane) was efficiently synthesized by reduction of the corresponding pyrilium salts obtained by treatment of selected flavanones and aldehydes with anhydrous HClO4. Cytotoxic effects on the human breast cancer cell line MCF-7 and antiestrogenic activity (only for compounds which resulted more active than tamoxifen (TAM)) on MCF-7 cells stimulated by 17beta-estradiol were evaluated. In vivo antiestrogenic activity and the relative binding affinity were also assessed. Some of the new compounds (4c, 4h, 4i and 4l) showed a biological activity in the micromolar range, and were more potent than TAM taken as the reference.

  DOI：

  10.1016/j.farmac.2004.09.006
• 作为产物：
  描述：

  6-(4-Methoxy-phenyl)-6H-chromeno[4,3-b]chromen-12-ylium; perchlorate 在 吡啶 、 甲酸 作用下， 反应 0.03h， 以70%的产率得到6-(4-Methoxy-phenyl)-6H,7H-chromeno[4,3-b]chromene
  参考文献：
  名称：

  Homopterocarpanes as bridged triarylethylene analogues: synthesis and antagonistic effects in human MCF-7 breast cancer cells

  摘要：

  A series of new compounds structurally derived from 6a,12a-dihydro-6H,7H-[1]-benzopyran-[4,3-b]-benzopyran (homopterocarpane) was efficiently synthesized by reduction of the corresponding pyrilium salts obtained by treatment of selected flavanones and aldehydes with anhydrous HClO4. Cytotoxic effects on the human breast cancer cell line MCF-7 and antiestrogenic activity (only for compounds which resulted more active than tamoxifen (TAM)) on MCF-7 cells stimulated by 17beta-estradiol were evaluated. In vivo antiestrogenic activity and the relative binding affinity were also assessed. Some of the new compounds (4c, 4h, 4i and 4l) showed a biological activity in the micromolar range, and were more potent than TAM taken as the reference.

  DOI：

  10.1016/j.farmac.2004.09.006

文献信息

• Homopterocarpanes as bridged triarylethylene analogues: synthesis and antagonistic effects in human MCF-7 breast cancer cells
  作者：Angela Rampa、Alessandra Bisi、Federica Belluti、Silvia Gobbi、Lorna Piazzi、Piero Valenti、Antonella Zampiron、Anna Caputo、Katia Varani、Pier Andrea Borea、Maria Carrara

  DOI：10.1016/j.farmac.2004.09.006

  日期：2005.2

  A series of new compounds structurally derived from 6a,12a-dihydro-6H,7H-[1]-benzopyran-[4,3-b]-benzopyran (homopterocarpane) was efficiently synthesized by reduction of the corresponding pyrilium salts obtained by treatment of selected flavanones and aldehydes with anhydrous HClO4. Cytotoxic effects on the human breast cancer cell line MCF-7 and antiestrogenic activity (only for compounds which resulted more active than tamoxifen (TAM)) on MCF-7 cells stimulated by 17beta-estradiol were evaluated. In vivo antiestrogenic activity and the relative binding affinity were also assessed. Some of the new compounds (4c, 4h, 4i and 4l) showed a biological activity in the micromolar range, and were more potent than TAM taken as the reference.